North Freedom native Chad Holloway went "all in" following his life's passion, and now he's cashing in with the job of his dreams.
The 28-year-old Reedsburg resident has made his living as a senior writer for PokerNews.com since October 2010. He likens the website to "the CNN of the poker world."
Writing daily poker articles for the website is one of his duties, but Holloway also covers major poker events about once a month. He gets to stand in the background of famous poker stars such as Daniel Negreanu and Madison native Phil Hellmuth as he blogs the live action.
"That's my favorite part of the job because it allows me to travel," he said, adding that he's been to Argentina, the Bahamas, Los Angeles and Las Vegas in the last eight months.
But the job also is a big challenge, he said. Some days will be 14 hours of work as he follows the action at the poker tables, Holloway said.
"At times it's grueling and you're tired, but when you really have a passion, or love it like I do, there's nothing else I'd rather be doing," he said.
That passion has been tested in the last few years.
Holloway had to give up other career paths to follow his dreams. That story is something that's in high demand, he said.
"I get asked all the time, people always want to know the story of, ‘How'd you get into that? How'd you get that gig?'" Holloway said.
He said it all started when he dropped out of law school at Tulane University to pursue a career knew he'd enjoy.
"After two semesters of law school, I just did not have a passion for it at all," Holloway said. "I realized I would be very unhappy doing that for the rest of my life."
While studying law in New Orleans, he found a passion he wanted to pursue at Harrah's Casino. Holloway said he turned $400 of spare cash into nearly $2,000 in his first week at school.
He knew starting a career as a poker player was unlikely, but he wanted to stay in the industry. Holloway found a Craigslist job to write about poker and did so for about a year, building up a portfolio of work.
"That was my first foot in the door for poker writing," he said.
But at only $12 an article, it wasn't a career. Holloway picked up other odd jobs along the way to support himself.
In January 2009, he took a leap and emailed all the poker industry personalities he knew and asked them how they got the jobs they had. The response was not encouraging.
"The overwhelming response that I got back was that you just don't make it in this business," Holloway said. "But I did get one back that said you're best bet is to basically work freelance and submit your articles to publishers and see if they like your stuff. I took that to heart."
Holloway said he knew it was important to find a niche to get noticed, so he started writing articles about fantasy poker, which is like fantasy football. The publisher of Pro Poker Magazine liked his column and picked him up in May 2009.
That summer Holloway was able to land a freelance job with Bluff Magazine to cover the World Series of Poker in Las Vegas, the biggest poker event of the year. He described it as an unpaid internship since he had to pay his own way and the small wage he made was only enough to make it a break-even experience financially.
Believing his poker writing days likely would be limited to covering the WSOP, blogging and writing his fantasy poker column, Holloway got his teaching certificate and was student teaching in the spring of 2010 at Sauk Prairie High School.
He applied for a freelance job with PokerNews to cover the WSOP in 2010. To his surprise, he got the job. But it wasn't an easy decision to leave a stable career in teaching.
"Just like the game of poker, it was a gamble," Holloway said. "In hindsight I'm so glad I made that choice."
His father, Larry Holloway, is one of the people who gave him some advice with the decision.
"I always told him he could do anything in life he wanted and he would succeed at it," he said, adding that he supported his decision to go to the WSOP. "I'm truly proud of him."
When the WSOP was over at the end of summer, Holloway emailed the editor-in-chief at PokerNews, Matthew Parvis, to see if there was other freelance work he could do. He was happy to learn there was an opportunity for him to cover a poker tournament in Argentina in September.
When he was in the Southern Hemisphere, a longtime PokerNews writer quit. Holloway was offered the full-time job.
"It was really a no-brainer for me," he said. "It was the opportunity I always hoped for as far as breaking into the industry. It just doesn't happen. Luckily for me, it did."
Offering Holloway the job was a no-brainer for Parvis, who said he met him at the WSOP in 2009.
"Chad brings a very unique attitude to the table," Parvis said. "Working events can be very tough with long hours and it can really be a grind.
"Chad has the ability to take those things with a grain of salt," he added. "He's really positive all the time."
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